Inside Sylvester Stallone's History Of Failed Relationships

Sylvester Stallone has been in several rocky relationships over the course of his life, to say the very least. Although the action star seemingly found the love of his life in his current wife, Jennifer Flavin, their long-standing union also went through a rough patch in its early days. The couple started dating back in 1988 when Flavin was a regular 19-year-old girl, and Stallone was a 40-something megastar. Although they seemed happy, over the next few years things took a turn for the worse. In 1994, Flavin confessed to People that Stallone had abruptly dumped her in a rather deplorable fashion: "He sent me a six-page handwritten letter, in pen. It was pretty sloppy." Despite the considerable length, the "Expendables" star conveniently left out the fact that he had cheated on her with supermodel Janice Dickinson, and Flavin had to learn the truth from her own modeling agent. 

If that wasn't bad enough, Stallone couldn't bring himself to hand her the letter, so he sent it over through FedEx. During a 2024 appearance on Sean Hannity's Fox News show, "Sean," the actor admitted that he wasn't proud of how he ended things with Flavin, noting, "In my profession, or my life, I should say, the way I've been structured is my history with relationships is an abomination." Stallone continued, "I couldn't live without her. She is my everything, my sun, my moon, everything." As a result, they ultimately got back together, tied the knot in 1997, and subsequently welcomed three children.

In August 2022, Jennifer Flavin filed to end her 25-year-long marriage to Sylvester Stallone. According to court documents obtained by People, the model claimed that her husband "has engaged in the intentional dissipation, depletion and/or waste of marital assets which has had an adverse economic impact on the marital estate." As a result, Flavin requested the court to bar Stallone from using any of their marital assets for his own financial gain until they settled their divorce.  Additionally, she sought a greater portion of their shared assets in her settlement. Shortly after, a source informed People that the couple's decision to split had stemmed from a multitude of problems they just couldn't seem to get past. The insider noted that the spouses knew their marriage had stopped working a while ago and had decided to stay together for the sake of their kids. 

Ultimately, though, Stallone and Flavin couldn't stay apart for too long and found their way back to one another again a month later. At the time, a confidant revealed to People that Flavin wanted to end their marriage because she grew tired of her husband constantly ignoring her concerns. However, the "Rocky" star had turned over a new leaf and was willing to go above and beyond for her. Stallone touched on his feelings about their brief split during a 2022 interview with the Sunday Times, reasoning, "There was a reawakening of what was more valuable than anything, which is my love for my family. It takes precedence over my work, and that was a hard lesson to learn."

Sylvester Stallone's first wife, Sasha Czack, walked down the aisle with him in 1974. In the following years, they welcomed two sons, Seargeoh and Sage Stallone. During the couple's joint 1985 chat with People, Sylvester and Czack confirmed that medical professionals had diagnosed Seargeoh with autism and strongly urged them to institutionalize him. Although the parents admittedly took the diagnosis hard, they opted against following the medical advice and vowed to do their best for their son instead. However, Czack pointed out that Sylvester's hectic schedule prevented him from being a full-time parent, so she only asked for financial support and took on the main responsibility of raising their child herself. Elsewhere in the interview, the action icon confessed that Seargeoh's diagnosis had given them differing priorities, explaining, "It really was the turning point in Sasha's life." 

He elaborated, "Her dreams and aspirations have been rechanneled into dedicated research. [...] All of her priorities are geared toward finding a cure. There is no fun in the future that way." Although the couple first called it quits in 1978, they reconciled and only got divorced in 1985. At the time, rumors suggested that Sylvester had cheated with Danish model Brigitte Nielsen. Entertainment Weekly also reported that Sylvester's romance with Nielsen had an unusual start since she had sent a note to his hotel room containing her name and phone number and expressed her desire for a meeting. People added that Nielsen had included an explicit photo of herself, despite being married to another man.

Brigitte Nielsen and Sylvester Stallone stoked the infidelity rumors further by tying the knot in December 1985, mere months after his divorce from Sasha Czack was finalized. While appearing on OWN's "Where Are They Now?" the Danish model acknowledged that she was hesitant to marry Stallone from the get-go because they hadn't been dating for long enough to warrant such a serious commitment. However, she eventually gave in after much pleading from the "Creed" star. As a result, it's unsurprising that their marriage only lasted about a year and a half. Reports from the time hinted that Nielsen had been unfaithful with director Tony Scott while she was starring in his film "Beverly Hills Cop II." Additionally, an insider informed People that their relationship was another tragic detail of Stallone's life. 

"She is a real conniver and schemer," they remarked of Nielsen. "She made a fool of him publicly. She used him. I don't think he ever thought anyone would get the better of him, and she did. He became a stepping-stone for her career." It's worth noting that, although the celebrity couple shared the screen twice during their short-lived union, in "Rocky IV" and "Cobra," Nielsen's Hollywood career didn't exactly reach new heights afterward. And the Danish star reckoned her ex-husband was to blame. Nielsen proclaimed on "Where Are They Now?" that she was "blacklisted" from the entertainment industry in the aftermath of their split and had to move back to Europe after being consistently unable to land gigs. 

About a month before Sylvester Stallone infamously called things off with Jennifer Flavin in a letter he FedExed over to her, the woman he was having an affair with, Janice Dickinson, gave birth to her daughter, Savannah Dickinson. In Janice's 2002 memoir "No Lifeguard On Duty," she detailed that she had sex with three men around the week of conception: Her boyfriend, Michael Birnbaum, Stallone, and an unnamed guy who was in Bette Midler's friend circle. However, the supermodel had a hunch that the child she was carrying was the "Rambo" star's. Thus, Stallone committed to their relationship and reportedly even popped the question. 

However, when Savannah was about a month old, the actor learned the child wasn't his after conducting a DNA test. According to Janice, he broke up with her by quipping, "Send my regards to Mr. Birnbaum' — and with that he stood up," as she wrote, per The Standard. The supermodel included some of the last words he ever said to her: "'We had a good run, Janice. Say nice things about me and I'll say nice things about you.' And then he turned and walked out." 

While the Hollywood legend made his way right back to Flavin, she was understandably devastated by his betrayal. During the couple's 1985 chat with People, the model shared that she, too, had been planning a future with Stallone right before he left her for Janice. In fact, the actor and Flavin had even made up their minds about when they wanted children and started narrowing down names for them.

After a then-48-year-old Sylvester Stallone ended things with Janice Dickinson, he quickly struck up a romantic connection with 22-year-old model Andrea Wieser. However, their relationship didn't go the distance because the "Suicide Squad" star then laid his eyes on 25-year-old supermodel Angie Everhart. As she asserted to People in a 1995 interview, Stallone was completely floored after seeing her grace the cover of In Fashion magazine, so he reached out to Everhart to help establish her Hollywood acting career by connecting her with a movie producer. However, things only turned romantic after they ended up at the House of Blues in Los Angeles, and their mutual friends brought the two of them together. The actor popped the question after just a few weeks of courtship in April 1995. 

Sadly, though, they went their separate ways two months later. At the time, the Tampa Bay Times reported that Stallone had become overly controlling by trying to dictate his new wife's outfits and meals. In fact, in a 2019 Facebook post, Everhart disclosed that he had also taken control of her breast augmentation surgery. The model requested her doctor bring her breasts to a C cup, but Stallone believed that a double D was more appropriate. So, while she was sedated, he supposedly asked the surgeon, who was also his friend, to go against her wishes, and he obliged. Unfortunately, Everhart had to endure loads of health issues over the years because of the implants. Although she later briefly joined Kevin Costner's relationship history, the model ultimately found the one in Carl Ferro.